Synthesis of perfluoroalkylated sugars catalyzed by rabbit muscle aldolase (RAMA)

Abstract

Perfluoroalkyl iodides [R_fI: Cl(CF₂)₄I, Cl(CF₂)₆I, C₈F₁₇I] react with acrolein diethyl acetal catalyzed by sulfinatodehalogenation reagents to produce 2-iodo-3-(perfluoroalkyl)propanal diethyl acetal 1, which is converted into (E)-3-(perfluoroalkyl)acrolein diethyl acetals 2 on treatment by base (KOH–MeOH). 3-Perfluoroalkyl-D-glyceraldehyde diethyl acetals 3 are produced through the asymmetric dihydroxylation (AD) of compound 2. Then 3 are easily hydrolyzed to 3-perfluoroalkyl-D-glyceraldehydes 4, which could react with DHAP catalyzed by RAMA and further acid phosphatase to form 6-C-perfluoroalkyl-D-fructose, which is a novel sugar and surfactant.